2,2,2-Trifluoroethanol → HCID 86753152, compound

HRID 2395155Notes

Reaction equation

HRID 2395155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH3:24])([CH3:23])[C:8]3[C:13]([O:14][C:15]=2[C:16]=1CC([O-])=O)=[CH:12][C:11]([O:21][CH3:22])=[CH:10][CH:9]=3.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:49](=[O:52])(O)[O-:50].[Na+].C(O)[C:55]([F:58])([F:57])[F:56]>CN(C)C=O.[Pd]>[F:56][C:55]([F:58])([F:57])[C:49]([OH:50])=[O:52].[CH3:22][O:21][C:11]1[CH:10]=[CH:9][C:8]2[C:7]([CH3:24])([CH3:23])[C:6]3[C:15]([O:14][C:13]=2[CH:12]=1)=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3

Participants

7

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86753149HCID 86753149, compound

Product 1

HCID 86753152HCID 86753152, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.47g of benzyl 5-[(Nα -benzylbxycarbonyl-NG -(2,2,5,7,8-pentamethylchroman-6-sulphonyl)-L-arginyl-glycyl-4-O-tert-butyl-L-aspartyl-L-valyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 25 ml of trifluoroethanol was stirred under hydrogen for 2 hours in the presence of palladium/charcoal (10%). Thereafter, the catalyst was filtered off and the filtrate was brought to dryness, The residue was taken up in 20 ml of dimethylformamide together with 0.34 ml of diisopropylethylamine. The solution obtained was added dropwise within 20 minutes to a solution of 0.66 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate in 50 ml of dimethylformamide, whereupon the mixture was stirred at room temperature for 1 hour. Subsequently, the majority of the solvent was removed in a vacuum, whereupon the concentrate obtained was poured into dilute sodium bicarbonate solution. The resulting precipitate was filtered off, washed with water and dried. This crude product was dissolved in a mixture of 20 ml of trifluoroacetic acid, 0.5 ml of water and 0.2 ml of phenol. The solution was left to stand at room temperature for 1 hour and then concentrated. The residue remaining was digested with ether and lyophilized from glacial acetic acid. After purification by HPLC (C-18 phase; gradient: water/ethanol with 0.1% trifluoroacetic acid) 75 mg of 4,5-cyclo-[acetyl-L-arginyl-glycyl-L-aspartyl-L-valyl-aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene trifluoroacetate(4,5-cyclo-[acetyl-SEQ ID NO:2-aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene trifluoroacetate) were obtained; IR 3364, 2965, 2841, 1664, 1577 and 1497 cm-1 ; MS: 767 (M+H)+.

Workup

  1. filtrationThereafter, the catalyst was filtered off
  2. customThe solution obtained
  3. customSubsequently, the majority of the solvent was removed in a vacuum, whereupon the concentrate
  4. customobtained
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. dissolutionThis crude product was dissolved in a mixture of 20 ml of trifluoroacetic acid, 0.5 ml of water and 0.2 ml of phenol
  9. waitThe solution was left
  10. waitto stand at room temperature for 1 hour
  11. concentrationconcentrated
  12. customAfter purification by HPLC (C-18 phase; gradient: water/ethanol with 0.1% trifluoroacetic acid) 75 mg of 4,5-cyclo-[acetyl-L-arginyl-glycyl-L-aspartyl-L-valyl-aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene trifluoroacetate(4,5-cyclo-[acetyl-SEQ ID NO

Sources & evidence

ORD record
ord-1b830c29ed874b9a85aec2b9d90d3c2c
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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